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Call Confessions: Born To Be A Cuckold Cross Dresser

Have you ever heard that phrase ‘Don’t ever judge a book by it’s cover’? A cross dresser is often the same. Your eyes may tell you one thing, but the truth may be a different story. You’d probably never guess my new friend ‘Pee Wee’ would be a cross dresser. He’s 6’3, 250 lbs…..and just the sweetest. His wife dominated him for years and it molded him into the most gentle darling and easy putty in the hands of a Mistress like me! Even more than that, someone who might just end up being a fantastic cuckold.

One Woman’s Cast-Off….

Pee Wee’s wife eventually moved onto bigger, sexier cock. But who could blame her? He was only able to offer one inch for every year I’ve been at LDW. (Let’s count them: 1-2-3-4!) That’s right, Pee Wee’s sad four incher was never going to be able to wow a woman or get her moaning. That ex-wife of his told at least a few of her friends about Pee Wee’s inadequacy, and the humiliation left him wanting even more. Nervous around dominant women and completely submissive, leg worshipping Pee Wee might be seen as a failure. His wife cast him off and moved on, but is Pee Wee really a failure?

A Cuckold In The Rough….

I think we could all agree that masculinity is not his strong suit. But Pee Wee is the perfect candidate to be repurposed as a cuckold. He thrives on serving women and would be a loyal pleasure provider in other ways besides as a husband. Humiliated all his life, Pee Wee has alot of untapped potential for the dominant woman who can recognize him as a gold mine. She just has to look a little deeper. I wish I could get my hands on Pee Wee, myself! It would be so fun to play Panties In A Pile with him and turn him into a party toy for my lovely lady friends that would not hesitate to laugh and giggle as he sniffs panties and then takes a naughty strap-on at the end.

I hope I get to play with Pee Wee for a long time!


* Call Confessions is not a surprise blog, and featured callers have been notified. Any names I use are changed to protect the not so innocent. *

7 comments to Call Confessions: Born To Be A Cuckold Cross Dresser

  • Petey cream puff

    That’s hot!!!! I sooo want this to happen to me for real but I’ve had no luck. I’d love to have my masseuse do this to me. She has hot friends that have had parties where they try on women’s clothes. I asked her friend who does this about it and what she thought about guys doing this and she said not many if any. 😢😟. It’s not about having sex for me. I’d love to have them make me try on dresses with 15-20 of masseuses gfs. This is what I want in relationship mistress. I’ve always been scared/shy about coming out but I did with her. She even told me this is who I am and become. I hate wearing guy clothes. Seeing women wear sexy tops/blouses/dresses/boots/yoga pants is such a turn on that I’ve started to wear them. If they can so can I. I want to be her cream puff. She told me I need to tell girl I’ve been friends with for 5 years as she thinks she already suspects this. She’s right!!! I’m sure it will raise eyebrows with her but at this point and my age I’m starting to not care. Both have taken control of what I spend and if I spend foolishly they both will kick my butt. She knows a lot about me except this and she told me she wants to make me more well rounded and know more about me. Do you think her asking this that she wants to control me? I do.

    • Amber

      You need to be honest with her about what you really want and at the same time, not resist what she wants to do with you, Petey! That’s how you’re going to be happy!

  • Awww poor Pee Wee he was born with everything a woman needs except a package in his pants. It’s like Nature is playing a cruel joke on him and women. Nature forgot one important part of the man. At least with someone like me who is short, thin and small it all makes sense but with Pee Wee it’s one big tease

    I hope he does have the honor of serving you for a long time Mistress Amber.

  • Mr. Thimble

    Wow! Do you think with a dick that small it was just inevitable he’d become a cuckold? That’s a frightening thought because his dick is actually a bit *bigger* than mine. And it sounds like his body is so much bigger and sexier that it almost makes mine look like a sissy already. I’m not destined to become a cuckold little pee wee too, am I?

  • Sissy April Nicole

    Either a cuckold a sissy a crossdresser or just a loner man with no life is the future of the tiny penis unendowed male hope you have nice legs to strut!

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